Born in Itta Bena, Miss., in 1936, Barry likes to invoke his Mississippi Delta roots. But his family, without his father, moved to Memphis when Barry was four. He grew up there, where he graduated from high school and LeMoyne College. He got his first taste for public confrontation and media notoriety during the city's 1958 bus desegregation drive. He subsequently abandoned graduate studies in chemistry at Nashville's Fisk University to join the civil rights movement full-time. Barry was elected the first chairman of SNCC (Student Nonviolent Coordinating Committee) and came to Washington in 1965 to open up a local chapter. He never left, and became the most dominant politician in the nation's capital since Boss Shepherd 100 years earlier.
Barry moved easily from 1960s street demonstrations into 1970s elective politics, switching from dashiki to business suit to fit his political needs. Barry served on the city's first elected school board (including a stint as Board president), and the first elected city council, and, in 1978, became the second person ever elected mayor in D.C. He held that office for 12 years, until his 1990 drug arrest and misdemeanor conviction in a highly charged trial forced him to step down.

After serving a six-month federal prison term, Barry reclaimed the office in 1994. But in 1995, early into his fourth term, Congress stripped Barry of most of his power, handing leadership of nine city agencies to a control board. In May 1998 Barry announced he wouldn't run again and in January 1999 handed the seal of the District of Columbia to incoming mayor Anthony A. Williams, who had been his CFO. This seemed to signal the end of the Barry era. But less than eight months later, rumors began circulating that Barry would seek an at-large council seat. Barry quashed them the following June, announcing that rather than seek office again, he'd devote his energies to reducing violence in the District (a year later, he'd seemingly done little toward that aim). But the rumors of 1999 became fact a few years later: In 2002, he campaigned for an at-large council spot. His attempt ended in mini-scandal: Late one night in March of that year, US Park Police found Barry idling his Jaguar at Buzzard Point in Southwest. Barry reportedly swallowed something as a US Park Police officer approached and had a powdery substance under his nose. Drug dogs sniffed out trace amounts of crack and marijuana in his car. He bowed out of the race in early April.

To his constituents, the flamboyant Barry is beloved as a jobs provider; to his critics, he is blamed for a bloated, inefficient bureaucracy that virtually bankrupted the city in the 1990s. Barry has acknowledged his addictions to cocaine, alcohol, and sex, and he turned his recovery into a political asset in his 1994 comeback. He has not admitted his addiction to the media, and to power.

The man known as the Mayor-for-Life has enjoyed a better reception in the private sector than he had in Congress: He's done lobbying work for a private-prison company and consulted on municipal bonds for an investment-banking firm.